198215-76-8

Basic information

• Product Name: 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose
• CAS NO: 198215-76-8
• Molecular Weight: 534.563
• Mol File: 198215-76-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose(198215-76-8)
• EPA Substance Registry System: 4,5-di-O-benzoyl-2,3-O-((1R*)-1-benzyloxymethylethylidene)-β-D-fructopyranose(198215-76-8)

Safety Data

• Hazardous Substances Data: 198215-76-8(Hazardous Substances Data)

Upstream product

• 198215-71-3 4,5-di-O-benzoyl-1-O-benzyl-2,3-O-isopropylidene-β-D-fructopyranose 
• 60885-00-9 1-O-benzyl-2,3:4,5-di-O-isopropylidene-β-D-fructopyranose 
• 96520-09-1 (3aS,6R,7R,7aS)-3a-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 
• 100-39-0 benzyl bromide 
• 22539-93-1 3-benzyloxypropanone 

Downstream Products

• 198215-81-5 Sulfamic acid (2R,3aS,5aR,8aR,8bS)-2-benzyloxymethyl-2,7,7-trimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-ylmethyl ester 
• 198215-79-1 ((2R,3aS,5aR,8aR,8bS)-2-Benzyloxymethyl-2,7,7-trimethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-methanol 
• 198215-78-0 (2R,3aS,6R,7R,7aS)-2-Benzyloxymethyl-3a-hydroxymethyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol 

Relevant articles and documents

Synthesis of hydroxylated derivatives of topiramate, a novel antiepileptic drug based on D-fructose: Investigation of oxidative metabolites

To corroborate the structures of two monohydroxylated metabolites of topiramate (1), we synthesized four monosaccharide derivatives from D- fructose: 4,5-O-[(1R*)- and 4,5-O-[(1S*)-1-hydroxymethylethylidene]-2,3-O- isopropylidene-β-D-fructopyranose sulfamates (2a and 2b); 2,3-O-[(1R*)- and 2,3-O-[(1R*)-1-hydroxymethylethylidene]-4,5-O-isopropylidene-β-D- fructopyranose sulfamates (3a and 3b). The route to 2a and 2b was brief and straightforward, while that to 3a and 3b was more involved. In the latter case, the D-fructose bis-acetal 10 was benzylated and converted to a monoacetal dibenzoate (14) (50% yield), which was then transacetalized to give a mixture of 4,5-dibenzoyl-2,3-O-[(1R* and 4,5-dibenzoyl-2,3-O-[(1S*)- 1-benzyloxymethylethylidene]-β-D-fructopyranose (16a and 16b) (22%). The individual diastereomers were separated and processed via ester saponification, acetonation, sulfamoylation, and hydrogenolysis into 3a (36%) and 3b (27%). Structure 2b was confirmed for one oxidative metabolite, but the other metabolite was found not to correspond with either 2a, 3a, or 3b. On the basis of CI-MS and 1H NMR data, a (2-hydroxy-1,4-dioxano)pyran structure, 4, is proposed for this unidentified metabolite.